CARBONYL COMPOUNDS QUESTION BANK

Question 1

a) Write a note on following name reactions:

i) Ozonolysis
ii) Rosenmund’s reduction
iii) Stephen’s reaction
iv) Clemmenson’s reduction
v) Wolff- Kishner reduction
vi) Aldol condensation
vii) Cross aldol condensation
viii) Cannizzaro’s reaction
ix) Etard Reaction.
x) Benzoin condensation
xi) Perkin’s reaction
xii) Kolbe’s electrolytic reduction
xiii) HVZ reaction
xiv) Decarboylation reaction
xv) Grignard reaction with carbonyl compounds

b) How will you distinguish the following pair of compounds?

i) Formaldehyde and acetaldehyde
ii) Acetaldehyde and acetone
iii) Formaldehyde and benzaldehyde
iv) Acetaldehyde and benzaldehyde
v) Acetone and benzaldehyde
vi) Formaldehyde and formic acid
vii) Formic acid and acetic acid
viii) Formic acid and benzoic acid
ix) Acetic acid and benzoic acid
x) Acetic acid and phenol
xi) Phenol and benzoic acid
xii) Acetaldehyde and acetic acid
xiii) Acetone and acetic acid
xiv) Acetone and phenol

Question 2

a) Which is more reactive towards nucleophilic addition? And explain why?

i) Acetaldehyde or acetone
ii) Acetaldehyde or benzaldehyde
iii) Acetaldehyde or propanal
 b) Formic acid is a carboxylic acid, yet answers Tollen’s test and Fehling’s test. Explain
c) Carboxlic acids do not give the characteristics reaction of carbonyl group. Why?
d) Compare the acid strength of carboxylic acids using inductive effect.
e) Which is strong acid and why?
i) Formic acid or acetic acid
ii) Acetic acid or benzoic acid
iii) Acetic acid, chloroaceticacid, dichloroacetic acid, trichloroacetic acid
iv) Chloro acetic acid, nitro acetic acid, Cyano acetic acid, fluoro acetic acid.
v) Benzoic acid, p-nitrobenzoic acid, p-methyl benzoic acid, phenol.
f) Acetic acid undergoes HVZ reaction. But formic doesnot. Why?
g) Benzoic acid is stronger than acetic acid, but weaker than formic acid. Why?
h) Fluorine is more electronegative than chlorine but p-fluorobenzoic acid is weaker acid than p-
chlorobenzoic acid. Explain.

Question 3

a) Give balanced chemical equations for the following;

i) acetaldehyde with phenyl hydrazine
ii) benzaldehyde with hydrogen cyanide
iii) benzoic acid with phosphorous pentsachloride
iv) Benzaldehyde with hydroxyl amine
v) Benzaldehyde with 50% sodium hydroxide solution
vi) Benzoic acid is treated with a mixture of conc.sulphuric acid and conc.nitric acid
vii) Methyl magnesium iodide is treated with CO 2 and the product is hydrolysed in acidic
medium
viii) Acetaldehyde is treated with hydroiodic acid in presence of red phosphorous
ix) Calcium acetate is subjected to dry distillation
x) Benzaldehyde is treated with sodium bisulphate
xi) Formaldehyde is treated with ammonia
xii) Acetaldehyde with hydroxylamine
xiii) Ethene with ozone
xiv) But-2-ene with ozone
xv) But-1-ene with ozone
xvi) Acetylene with water in the presence of dil.acid and mercurous ion catalyst.
xvii) Propyne with water in the presence of dil.acid and mercurous ion catalyst
xviii) Dimethyl cadmium with acetyl chloride
xix) Conversion of ethy acetate to acetaldehyde
xx) Dry distillation of calcium acetate and calcium formate
xxi) Dry distillation of calcium formate
xxii) Reaction of acetaldehyde with iodine and alkali
xxiii) Reaction of acetone with iodine and alkali
xxiv) Oxidation of methanol to formaldehyde
 xxv) Oxidation of ethanol to acetaldehyde
xxvi) Oxidation of isopropyl alchol to acetone
xxvii) Acetaldehyde with ammonia
xxviii) Acetone with ammonia
xxix) Benzaldehyde with nitrating mixture
xxx) Benzaldehyde with bromine solution
xxxi) Acetic acid with ethanol in the presence of conc.sulphuric acid
xxxii) Oxidation of ethanol to ethanoic acid’
xxxiii) Reduction of acetaldehyde to ethanol
xxxiv) Reduction of formaldehyde to methanol’
xxxv) Reduction of acetone to isopropyl alcohol
xxxvi) Oxidation of formaldehyde to formic acid
xxxvii) Oxidation of acetaldehyde to acetic acid
xxxviii) Oxidation of benzylalcohol to benzoic acid
xxxix) Oxidation of benzyl alcohol to benzaldehyde
xl) Oxidation of benzaldehyde to benzoic acid
xli) Hydrolysis of methyl cyanide to acetic acid
xlii) Reaction of methyl magnesium bromide with carbon dioxide to get ethanoic acid
xliii) Reaction of acetic acid with sodium bicarbonate
xliv) Acetic acid with sodium hydroxide
xlv) Acetic acid with thionyl chloride
xlvi) Acetic acid with ammonia and heating
xlvii) 2 moles of acetic acid to acetic anhydride
xlviii) Reaction for the conversion of sodium acetate to methane
xlix) Reaction for the conversion of sodium proponoate to ethane
l) Nitration of benzoic acid
li) Sulphonation of benzoic acid

b) How will you effect the following conversions?

i) ethanol to acetone
ii) benzene to acetophenone
iii) benzoic acid to benzaldehyde
iv) acetaldehyde to acetone
v) formic acid to formaldehyde
vi) ethanol to but-2-en-1-al (aldol)
vii) acetaldehyde to acetamide
viii) benzoic acid to benzene
ix) benzene to benzoic acid
x) ethyl chloride to acetaldehyde phenyl hydrazone
xi) toluene to benzoic acid
xii) propanone to propene
 xiii) benzaldehyde to benzophenone
xv) Ethanal to propanal
xvi) Acetaldehyde to formaldehyde
xvii) Acetic acid to formic acid’
xviii) Methyl chloride to acetone
xix) Benzoic acid to aniline’
xx) Acetic acid to methyl amine
xxi) Acetylene to acetic acid
xxii) Propyne to isopropyl alcohol
xxiii) Ethyl cyanide to ethanoic acid
xxiv) Benzene to methyl benzoate
xxv) Benzene to p-nitrobenzoic acid
xxvi) Benzene to phenyl acetic acid

Question 4

a) An aliphatic unsaturated hydrocarbon (A) when treated with HgSO 4/ H2SO4 yields a compound
(B) having molecular formula C3H6O. (B) on oxidation with conc. HNO3 gives two compounds (C)
and (D), compound (C) when treated with PCl 5 gives compound (E). (E) when reacts with ethanol
gives a sweet smelling liquid (F). compound (F) is also formed when (C) reacts with ethanol in
the presence of conc.sulphuric aicd’. Identify compounds A to F.

b) An organic compound A on treatment with ethyl alcohol gives a carboxylic acid (B) and
compound (C). Hydrolysis of (C) under acidified conditions gives (B) and (D). oxidation of (D)
with KMnO4 also gives (B). (B) on heating with calcium hydroxide gives (E) of molecular formula
C3H6O. (E) does not give Tollen’s test or Fehling’s Test , but forms a 2,4-dinitro phenyl hydrazone
. Identify the organic compounds A to E.

c) A ketone A( C4H8O) which undergoes haloform reaction gives compound (B) on reduction. (B) on
heating with conc.sulphuric acid at 1700 C gives a compound (C). compound (C) forms ozonoid
D. D on hydrolysis with Zn dust gives only (E). Identify the organic compounds A to E.

d) An organic compound A on treatment with acetic acid in the presence of sulpuric acid produces
an ester B. A on mild oxidation gives C. C with 50% KOH followed by acidification with HCl
generates A and D. D with PCl 5 followed by reaction with ammonia gives E. E on dehydration
produces hydrocyanic acid. Identify compounds A to E.

e) An alkene A of molecular formula (C 5H10) on ozonolysis gives a mixture of two compounds. B and
C. compound B gives positive Fehling’s test and also reacts with iodine and alkali. Compound C
does not react with Fehling’s solution, but forms iodoform. Identify the compounds A to C.